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The craving for killer views has inspired many homeowners to forsake their ground-bound abodes for something that shows a little sky. When Chicago businessman Michael Alper decided to trade in his 1894 Gold Coast megahouse for a lakeside flat, he wanted the most dazzling vistas to be the ones from his home office, because, he reasoned, "that's where I spend most of my time."

Moving also marked a new chapter in his life. After he and his wife, Pamela, finished an unstinting historic restoration of their 25,000-square-foot home and filled it with Biedermeier antiques and contemporary art, she passed away. Eventually, Alper observes, "I was ready for something very different: someplace open, airy and much more modern, filled with comfortable furniture."

Alper scooped up a handsome Streeterville co-op overlooking Lake Michigan. The building had been designed by society architect and developer Benjamin Marshall in 1925. Back then, it was considered the city's premiere residence. Today, its cachet is intact. But a previous owner's gut job had "stripped the unit of too much character for Alper's liking," explains Chicago architect Dirk Denison, whom Alper hired to revitalize the austere flat.

The renovated apartment is deceptively simple, given the demands of the project. Alper was coming from a much larger home and owned a lot of furniture and art, including large-scale pieces that were taller and wider than most of the apartment walls. Then there was the issue of the home office, which he was determined to locate in what should have been the dining room, because it had the best views. Making the space work for his lifestyle and art was one momentous endeavor, while helping him figure out what to keep and where it would go was another. Denison focused on the former, while Alper's significant other, Sotheby's Midwest chairman Helyn Goldenberg, helped him find designer Michael Richman to navigate the latter.

Denison—a self-described "die-hard modernist," who is locally acclaimed for his clean-lined work—thought it would be effective to give the apartment new architectural vigor by "returning the rooms to their richly detailed neoclassical roots, then updating them with targeted contemporary interventions." Goldenberg, who also lives in the building, helped with the first part of the plan, since moldings and millwork in her apartment were intact. Denison copied her originals to detail Alper's rooms anew. He also executed maneuvers the original builder couldn't have imagined would ever be necessary, first raising the door frames as high as the towering windows. Then he installed a sleek, floating glassand- onyx fireplace screen suspended on a lean stainless steel frame over half the living room wall.

Originally, Alper planned to cull most of the furniture for the apartment from his previous home. He owned plenty of pieces perfectly suited to the classical lines of the new apartment. But as work progressed, Denison added more contemporary flourishes. The already roomy foyer connecting the front and back areas of the home was expanded to become a 60-foot-long gallery to hold large art, and the former maid's room was transformed into a bar. White walls were replaced by Brazilian gumwood panels and pristine, gleaming glass display cabinets. Soon it became clear that "almost all of the owner's furniture was too formal for the updated architecture," explains Richman, "so it went to Sotheby's."

Then began a quest that occupied both clients and designers. Denison accompanied Alper and Goldenberg to Art Basel Miami, where the trio haggled to obtain the last available chair by American pop artist Richard Artschwager. When Goldenberg and Denison convinced Alper to make his office a double-duty space, just in case he wanted to entertain there, they snapped up a dozen midcentury stacking chairs in Belgium. On trips to New York with Richman, they found more midcentury pieces, including a pair of Andre Sornay armchairs and a Silvio Cavatorta desk. Goldenberg pulled in the quirky Warren McArthur chair in the bar from a dealer who specializes in the designer's work. And after scouring stores worldwide, Richman found the perfect vintage Danish sofa to unify the living room—a steel and leather number by Fabricius & Kastholm—at Andrew Hollingsworth in Chicago.

Installing Alper's possessions was as labor-intensive as accumulating them. "Some of the artworks were so gigantic that they had to be hoisted in through the front window, so it was critical to hang them in the right spot the first time around," points out Denison. He created a complete set of elevations for the apartment, reducing photos of every piece to scale and popping them into place on the drawings. Siting the art went flawlessly—save for one piece: At ten feet four, Gursky's image of the Shanghai Grand Hyatt was two inches taller than the wall trim, so, rather than cutting the trim, a crew leaned it at an angle to gain extra inches.

Despite the team's enthusiastic treasure hunt, there were still a few spots to flesh out after everything arrived. Richman filled them in with ingenious pieces of his own design. In the living room, his playful Over Easy chair, inspired by Jean Royère's Oeuf and covered in downy white shearling and worsted wool, "mixed things up and added humor," says Richman, while his glass and steel Lumen table pulled together the other pieces and materials in the room. In the bedroom, rosewood nightstands based on an Andre Sornay design bridge a decorative gap between the vintage Italian desk and new custom-made bed.

Today, Alper's revamped home is fully fleshed out, and all the rooms are comfortably furnished. But they're far from filled. "It's not done yet and may never be," confides Goldenberg. "Every place you live should be a work in progress."

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Alper did not like the apartment's recently installed kitchen, but it seemed wasteful to gut it. The pure white, virtually seamless, sharply lit kitchen was "too glaring, antiseptic and monolithic for Alper's aesthetic," explains architect Dirk Denison, "so we toned it down with cosmetic changes to make it a smart, urbane mix of elements." Denison's laundry list of tweaks included replacing the super-glossy laminate cabinet and drawer fronts with warm, whitepainted wood and turning cabinets over the sink into open floating shelves for dishes that could give the room hits of color. He also introduced modernizing stainless steel in a hood and backsplash (and in such appliances as the Wolf stove and Sub-Zero refrigerator). He replaced an ice-white marble island top with rich Black Beauty granite, and he upgraded dim incandescent fixtures to higher-quality, energy-efficient dimmer-equipped lighting. "The cost," Denison estimates, "was about 20 percent of a complete makeover."